Sasha And Malia Obama's Inner Circle Is Filled With Celebrities

Growing up with famous parents certainly meant Malia and Sasha Obama rubbed shoulders with a ton of celebs. In light of that, we're not exactly surprised that even after their father's presidency, the Obama sisters' inner circle includes more than a few famous faces. From the family members of other political figures to friends and close colleagues in the entertainment business, it's safe to say these two are very well connected. 

For starters, there's Jenna Bush Hager and Barbara Bush. As many will know, the Bush twins made a point of showing the Obamas around the White House ahead of their move to Washington. Of that, Michelle Obama previously said in an interview with Hager for "Today," that the girls had really appreciated how genuinely warm their predecessors had been towards them, and how they'd carved out time for the occasion. More than a decade later, Hager shared in an appearance on "Watch What Happens Live with Andy Cohen" that she and her sister had maintained contact with them over the years. "I reach out to the Obama girls, and, you know, vice versa ... there is a sisterhood, because it's so few of us," she mused. 

With the Bush sisters essentially ushering the Obama girls into their position as public figures in their own right, it's heartwarming to know they keep in touch. However, over the years, Sasha and Malia have struck up close bonds with a number of other celebrities, too. 

Sisterhood of the former first daughters aside, Sasha Obama also has a super close bond with Joe Biden's granddaughter, Maisy Biden – but not just because of the obvious. As Barack Obama shared in an episode of "Armchair Expert with Dax Shepherd," his youngest daughter struck up a lifelong bond with Maisy at school. He added that to this day, Maisy is one of Sasha's best friends.

Barack isn't the only one to have pointed to just how close the girls are, though. Back in 2019, Joe also spoke about their bond. As was reported by The Hill at the time, the now-president shared with a group of people that the reason he couldn't make an appearance at a Democratic Party event was because his extended family and the Obamas had been celebrating Sasha and Maisy's high school graduation. "Her best friend is Sasha Obama. Barack and Jill and the whole family, we had a whole get-together," he was quoted as saying. 

Speaking of the families being good friends IRL, it's worth noting that Maisy isn't the only one of Joe Biden's grandchildren that Sasha is close to. 10 years before their graduation, the Guardian reported Joe as saying that in the midst of the 2008 August convention, Maisy's older sister, Finnegan Biden, had informed him that she and then-7-year-old Sasha were planning a sleepover party for the Biden and Obama girls. "Sasha is already talking to Bawack," he recounted her saying. 

Malia Obama might not have been the one who got the ball rolling on the Obama-Biden sleepover, and she wasn't in the same year group as any of Biden's granddaughters. Even so, though, all signs seem to point to her being just as close with the family as her younger sister is. Case in point: in early 2023, she was spotted hanging out a few of the family's members. 

In images published by TMZ, Sasha could be seen hanging out with a group that included both Maisy and Finnegan Biden, as well as their youngest brother, Beau Biden Jr. The outlet reported that the group had been to lunch prior to the pictures being taken, and that they'd taken pictures together. 

It's not clear if, like Sasha Obama, Malia shared any extracurricular interests with any of the Biden girls. After all, according to People, Sasha had more of a penchant for drama class than her sporty younger sister. Nevertheless, speaking to "Today," the Biden grandkids had a ton to say about both Sasha and Malia helping them prepare for their grandfather's presidency. Finnegan, in particular, gushed, "Being able to see two of our friends, you know, navigate eight years of what was really difficult, and they did so, so beautifully ... I think we can only take advice from them." Talk about a close-knit unit! 

Outside of their friends in the political sphere, Sasha Obama is also close with an ex-"Real Housewives of Potomac" star's daughter. That'd be Skylar Jackson-Jordan, daughter of Charrisse Jackson-Jordan. 

That Skylar and Sasha are friends first came out back in 2017, when reports emerged that the former had been at the first daughter's 16th birthday party. Though the images themselves seem to have been scrubbed from the internet, Charrisse acknowledged the friendship not long after. Speaking to Bravo, the "RHOP" alum shared that Skylar and Sasha were in the same friend group, and couldn't help but gush over the first daughter. "Very nice girl. Beautiful girl at that. She could be a model, she's so beautiful," she said. 

On that note of the girls being in the same friend group, that certainly checks out. After all, in the same interview, Charrisse also revealed, "[Skylar] tried out for this lacrosse team and, oh, Joe Biden's granddaughter, I think, or somebody was on the team ... And I was like, 'Oh, really? That's who that was?'" Sure enough, in the joint Biden grandkids interview with "Today," Maisy shared that she had played lacrosse at school. It's not clear if Skylar and Sasha are still as close post-graduation, or whether she was ever as friendly with Malia Obama. 

Sasha Obama isn't the only sister to have friends connected to the entertainment business. In fact, thanks to Malia's high-profile new job as a writer-director, a number of celebrities have spoken about how much they loved working with her. That said, one name that really stands out is Donald Glover, who happens to have mentored her. 

Though Malia has spent years working towards her dream career in the film and TV industry, with various internships at well-known TV shows, in 2023, Glover revealed that he'd hired her as a writer. They'd previously worked together on his Amazon TV show, "Swarm," but in her role at his production company, Gilga, he shared that she would be creating a short film. On that, he got real with her, pointing out that her family name meant she was almost guaranteed to get more than her fair share of hate (and sure enough, Malia has faced a ton of "nepo baby" criticism). However, it seems he did everything he could to help her create something great. Malia's debut project, "The Heart," went on to be nominated for four awards, and even earned her the award for the best live action short at the 2023 Chicago International Film Festival. 

Suffice it to say, the threat of heightened pressure didn't scare Glover off, and he continues to believe in the former first daughter. Speaking to TMZ, he hinted that he wouldn't be surprised if she won an Oscar one day. 

Outside of Donald Glover, another famous face Malia Obama counts as a friend is "Caroline" rapper, Amine. According to the Daily Mail, the rapper — real name Adam Aminé Daniel — met the Obama's first born when she sought him out. Per the outlet, in a 2017 interview with i-D of their first meeting, he recounted, "I came offstage and a Lollapalooza security guard came up and said, 'Malia Obama would like to speak to you.' She was a super-normal, cool, regular American teen.'"

In the time since, the two have been seen out and about together at least once. In late 2023, pictures emerged of them going to dinner together were published by Daily Mail. Of course, that prompted speculation over whether they were a couple. True to form, though, Malia hasn't revealed if they are romantically involved or not — and frankly, we're not expecting that to change anytime soon. Friends or more, the point is that these two get on great, and likely have for years. 

Malia and Sasha Obama became public figures as kids, and as such, they're very much a part of celebrity life (even if a number of signs point to them not loving that). At the end of the day, we're not at all shocked that those in their inner circle are well-known in their own right.